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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Nitrogen versus Oxygen Group Protection in Hydroxypropylbenzimidazoles

Sutharsiny Indusegaram, Andrew G. Katsifis, Damon D. Ridley and Simone C. Vonwiller

Australian Journal of Chemistry 56(8) 819 - 827
Published: 18 July 2003

Abstract

In order to convert 1′H-benzimidazol-2′-ylpropanols into aryl ethers using Mitsunobu coupling, it was necessary to protect the benzimidazole nitrogen in the starting alcohols. Selective protection at nitrogen was achieved through N-benzyl derivatives, but attempts to protect the nitrogen directly through tert-butoxycarbonyl, acetyl, trityl, or tetrahydropyranyl derivatives were complicated either by selective reactions at oxygen or by the formation of bis-protected compounds. Transformations of some oxygen-protected derivatives are discussed, and in particular the conversion of the acetates of 1′H-benzimidazol-2′-ylpropanols to N-tetrahydropyranyl derivatives is described. Mitsunobu coupling involving the N-benzyl and N-tetrahydropyranyl derivatives and methyl 4-hydroxybenzoate were achieved, and thus afforded synthetic routes to the desired propylbenzimidazole aryl ethers.

https://doi.org/10.1071/CH03012

© CSIRO 2003

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